Happenstance
by Miguel51
Summary: Happenstance is defined simply as a coincidence, nothing more than a random event. But even the most innocent of coincidences can invite chaos of the highest order. Sequel to 'Kismet'.
1. Harbinger

**_HAPPENSTANCE_**

 **1 - Harbinger**

For the last fifteen years, life had been good to Rory. Hell, it had been better than good. Her life was near perfection, to be honest. She had a loving and successful husband. A brilliant and beautiful daughter. A family who loved and supported her. A rich and fulfilling career of lecturing about journalism and literature at universities all across the entirety of New England.

With all this in mind though, Rory couldn't help but feel ungrateful at her how crushed she felt at that moment.

 _It's funny how a little plastic stick that you pee on can completely ruin your morning,_ she rolled her eyes in disgust. It had been almost two years now, two whole years they'd been trying to conceive. Rory was starting to lose hope. _What am I_ _doing wrong_? _I've taken all the fertility drugs that Paris prescribed me! I'm the same_ _age as Mom was_ _when she had Billy! So why can't I_ _get pregnant? Why? It's not fair!_

"Damn it," Rory muttered under breath. She glared at the wastebasket where the offending negative pregnancy test had been thrown before kicking the entire thing over in frustration. She felt an odd sense of satisfaction at how the plastic receptacle bounced then fell over at the blow but that sensation was fleeting, gone as quickly as it had come. _Yeah, that was a mature response, Rory._

"Mom? You okay in there?"

"Yeah, I'm fine, Winn," she lied, not wanting to worry her only child. "Just accidentally kicked over the wastebasket, is all."

"Alright, if you say so," the teen stated, obviously not believing her mother but choosing to drop the subject. "Remember that the headmaster wants to speak with you and Aunt Paris this morning."

"I haven't forgotten, kiddo," an already tired Rory told the teenager. "I'll be down in five minutes."

"I love you but your five minutes starts now, mother," chirped Winifred before the echo of her saddle shoes could be heard clicking against the hardwood of the stairs. "Move it or lose it, Gilmore-Harrison!"

"Move it or lose it, Gilmore-Harrison," a heavy hearted Rory repeated to her reflection. _Time to get your shit together, Lorelai Leigh._

* * *

If there was one thing that Rory found reassuring, it was the fact that Chilton never changed. Sure, several members of the faculty had retired and been replaced by eerily similar younger counterparts but all in all, her old high school alma mater had remained the same.

"If that isn't the most pathetic expression of nostalgia I've ever seen, I don't know what is," a familiar voice teased from her left. "Hello, school chum."

"Hello, dear friend," Rory smiled at her old classmate. "How are you?"

"That's a loaded question, Gilmore-Harrison," warned Paris with a playful smirk. "You know why we're here, right?"

"Yeah," sighed the taller woman. "I had really hoped our girls would've worked their differences out already."

"They're our daughters, so I'm not surprised that they haven't," the blonde doctor stated. "Winny has your dislike of confrontation while my Milly has the infamous Geller stubborn streak. Thinking they'd work this idiocy out by themselves was probably wishful thinking."

"True but I honestly don't know what the headmaster thinks we can do about it," admitted Rory.

"Actually, I don't believe there is a lot you two can do about this," the headmaster commented from behind them.

"Then why have us come here at all, Headmaster Medina?" Paris turned to face their former English Literature teacher, an action that Rory was quick to follow. "Because, as you well know, my time is quite precious to me. Or rather, to my clients."

"Be nice," Rory told her friend, who scoffed in return. "But Paris does bring up a good point. Why bring us here to talk if you don't think we can help, Headmaster Medina?"

"We're all adults here, Rory," Headmaster Medina stated once he'd joined them at the bottom of the stairs. "Would it be too much to ask that you call me Max?"

"Not while we're in your place of work, Headmaster Medina," she told him, resolute. "Wouldn't it diminish your authority if one of your charges were to overhear me talking to you so casually?"

"I'd give up on trying to debate us on this one, headmaster," Paris cut in before he could reply. "Might I remind you that you're talking to the former captain and vice captain of the senior debate team here."

"Duly noted, you two," Max chuckled, hands raised up in mock surrender. "But back to the matter at hand." He gestured down the hall that led to his office. "Shall we?"

"Lead the way, Headmaster Medina," Rory agreed.

* * *

Following their meeting with Headmaster Medina, Rory and Paris went their separate ways with a promise to meet up later in the week. Although Rory felt a little guilty for not confiding in her friend about once again being unable to conceive, she also felt that her husband had the right to know before anybody else.

 _I am not looking forward to this conversation,_ Rory let out a resigned sigh while approaching her husband's office building. As she pushed her way inside via the revolving door, the prospect of having to once again witness Marty's face fall in disappointment caused Rory to hesitate. _I can't do this to him. Not right now. It'll ruin his entire day._

With this thought in mind Rory spun on her heel and left, deciding it would be best to put off telling her husband the bad news until Marty came home from work later that evening. Remembering that there was a coffee shop only two blocks away, Rory began the short trek towards where she could buy a cup of the life sustaining liquid.

Upon her arrival inside the coffee shop, Rory momentarily despaired at how many customers were ahead of her. When her turn in line finally came up, she ordered herself a double shot cafe latte then turned away to wait for her drink at one of the few open tables available. Seeing how busy it was at the moment, Rory decided to check her lecture notes over as she waited. With her tablet set atop the table she quickly became so engrossed in her work that Rory barely took notice of the waitress placing her order next to the former reporter.

In that time and space, every worry fell away from her. Her inability to conceive another child with Marty, along with all the pain and disappointment that it brought, was momentarily forgotten. The troubles that her beloved daughter Winifred was experiencing at Chilton faded into the background. Nothing mattered to Rory but the need to finish her lecture notes.

"It's good to see your ability to block out the world hasn't changed since Yale," a vaguely familiar voice stated, breaking her concentration.

"Excuse me?" she glanced up, only to blink in surprise at who was now addressing her. "Logan?"

"Hey, Ace," her college boyfriend greeted with a smirk. "Long time no see."

"Yeah, long time," an uneasy Rory agreed, desperately trying to ignore how hard her stomach was twisting itself into knots right then. It took the former reporter a moment to recognize this feeling of dread but once she did, a confused Rory couldn't help but wonder at its reason.

* * *

It wouldn't be until a few months time that Rory got an answer, and by then her entire world would be teetering on the edge of total collapse.

* * *

 **And so** **begins the sequel to 'kismet'. I hope you enjoy it.**


	2. Know Now Then

**2 - Know Now Then**

It had not been a very busy morning in the office for Marty. A few emails here, a couple of phone calls there but nothing that really required his immediate attention. The only reason he'd come in to work this early was to make some final preparations for the new head of legal's arrival, and even that only took about twenty to thirty minutes.

He frowned at the thought of the mysterious new head of legal, whom Marty had yet to meet. It had been almost a year since old Alan Smith had announced his retirement, only agreeing to stay on with the firm until Alan found himself a suitable replacement. Whoever he had chosen though must have impressed him because Alan was notoriously difficult to please. So difficult in fact that Alan had already refused three brilliant potential candidates for his position, all for various seemingly innocuous reasons.

"Mr. Harrison?"

His train of thought suddenly derailed, Marty glanced up at his administrative assistant, who was now patiently waiting in the doorway of his office. "Yes, Laura?"

"I'm sorry to disturb you, sir," she apologized. "But you wanted me to remind you about meeting with Miss Jacobs at noon."

"Oh, right," he nodded, grateful for the reminder. During his meandering thoughts, he'd lost track of time. "Thank you, Laura. What would I do without you?"

"Hire another assistant, I imagine," the bookish young woman deadpanned.

"I doubt they'd be as thorough as you with keeping my appointments in check," joked Marty while rising from his chair.

"No one is as thorough as I am, sir," Laura agreed. "It's why your wife insisted you hire me, remember?"

"That's true," he acknowledged with a nod.

"Speaking of your wife," his assistant segued while delicately adjusting the glasses perched on her nose to more comfortable position. "Someone mentioned they saw her enter the lobby this morning, only to turn around and head back into the street."

"Really? That's weird," Marty noted. "I'm pretty sure the only thing she had to do in the city today is meet the headmaster at Chilton. I wonder if it has anything to do with that?"

"Would you like me to text you if she shows up again, sir?" Laura inquired.

"No, that'll be fine," he shook his head. "If it was really important then Rory would've come up. I'll just ask her when I get home."

"Anything else, sir?"

"No, that's it. If I need anything though, I'll call to let you know, Laura. Thanks."

Without another word his assistant departed, an action which Marty soon imitated a moment after. On his way to the elevator his thoughts once again returned to the coming luncheon with Miss Jacobs, who was his soon-to-be new head of legal. Other than her first two initials and last name, not to mention the several recommendations from their newest branch in Seattle, the woman was almost a total mystery. Marty was pretty much Jon Snow in this situation, he knew nothing.

 _That's about change though,_ he mused to himself, the elevator doors opening for him to exit. _I wonder who this Miss Jacobs is? And why did she insist on meeting at a restaurant of all places?_

* * *

It wasn't that far of a walk from his office to the restaurant where Marty was supposed to meet with his enigmatic head of legal, though to be fair he hadn't tried all that hard to get information on this Miss Jacobs. Marty trusted Alan on finding his own replacement as the old fox had proven himself to be an impeccable judge of character. Still, all this secrecy was highly unusual.

"Hmm, not bad," Marty complimented the decor of the restaurant. It wasn't one of those overpriced places he expected a lawyer would want to meet, nor was it one of those generic chain locations that caused his wife's stepfather to roll his eyes derision. It was just the right mix of fancy and comfortable. _Rory and Winn would probably love it here. Of course, that would also depend on the quality of their food though._

"Good afternoon, sir," greeted the blonde hostess upon seeing Marty standing there in the entry way. "How are you doing today?"

"I'm fine, thanks," he politely returned.

"That's great to hear, sir," she smiled, seemingly genuine in her response. "Do you have a reservation?"

"Actually, I'm supposed to meet someone here," answered Marty.

"Ah, yes, now that you mention it, you fit the description one of our patrons gave us," the hostess nodded after eyeing him up and down for a moment. "If you'd follow me, sir. Your dining partner is already here, and awaiting your arrival."

 _Okay, this is weird,_ a wary Marty noted before doing what the hostess asked. She led him towards one of the beautifully lit booths beyond the tables, which had high ceilings and were separated by gorgeous wood cross panels that gave each booth a feeling of seclusion. If Marty wasn't happily married, he would've suspected that one of his friends had set him up on a blind date.

"And here we are," the hostess declared upon reaching the furthest booth, where an attractive woman who appeared to be in her late twenties or early thirties was seated alone. "Please be seated. Your server will be here shortly to take your order."

"Sorry that I'm late, Miss Jacobs," he apologized once they were alone. "But it took a little longer to walk here from the office than I expected."

"That's quite alright, Martin," his dining companion waved him off with a friendly smile. "I don't mind. It's not every day you meet up with an old friend."

"Excuse me?" Marty frowned.

"You don't recognize me, do you?" Her smile widened at his obvious confusion, turning from friendly to mischievous. "I'd be hurt if I hadn't been expecting it, so I'll let you off the hook this time, Martin. After all, it _has_ been about sixteen years since the last time we saw each other."

"You do look vaguely familiar, now that you mention it," he admitted after careful consideration. _Hmm, sixteen years? That would be about the time I_ _was just leaving Chicago with Rory...wait a second!_

"Oh, I see that you've finally connected the dots," the once tall gangly teenager grinned, genuinely pleased. "Mom says 'hi' by the way."

"And how is Kelsey these days? Doing well, I hope," he inquired.

"As well as she can be, considering the circumstances," she answered while taking a sip from her wine glass. "Her and Dad live over in Boston now, but you knew that already, right?"

"Yes, I did."

"You should visit them sometime soon. I know Dad would love it," the lawyer stated, a brief hint of sorrow in her pale blue eyes.

"Look, Riese, about your dad," a suddenly guilt filled Marty began at the mention of his former mentor, whom he hadn't seen in more than a decade.

"Let's not talk about that," she cut in with a shake of her head. "It's depressing and this is supposed to be a happy reunion, right?"

"Alright then," he agreed, not wanting to make her uncomfortable. "So...Jacobs?"

"Wow, you're really bad at this happy reunion stuff, ain't ya?" Riese quirked an eyebrow at him. Before he could apologize however, the lawyer grinned at him. "I'm only teasing you, Martin. It's my ex's last name."

That surprised Marty. "You got married?"

"Yup," she nodded. "Didn't last though. After about six months or so, I caught him banging his secretary, so that was the end of it. Kept his last name though. People who deal with our firm seem to take me more seriously when they don't know who my dad is, so I'm counting it as a win."

"Fair enough," conceded Marty.

"So what's good here?" Riese asked, her gaze now on the open menu in her grasp.

"I have no idea," he admitted in complete honesty. After all, it was his first time being in this particular restaurant.

The lawyer glanced up to meet his gaze, which quickly resulted in both of them to burst out laughing.

* * *

After their meal was finished Marty returned to the firm's offices with his new head of legal, where he introduced Riese to the other various department heads and their staff. When that was done he led Riese to where her new office had been set up.

"Sweet digs," the lawyer whistled upon entering the room. "Kind of sparse though."

"Yeah, it's a bit spartan," he began to apologize. "But-"

"It's fine, Martin," she cut in with a soft chuckle. "I can always hire a decorator or do it myself later. No biggie."

"I'll see if I can get the firm to pay for it," he offered. "Or, at least, split the cost."

"That's really very sweet of you, Martin, but also completely unnecessary," answered Riese with a genuinely appreciative smile. "Although it's great to see that you haven't changed a bit. So thoughtful. I always admired that about you."

"Um, thanks," Marty shrugged, not at all use to receiving compliments. Especially on things that just felt natural to him.

"Still not comfortable at being complimented, I see," his former mentor's daughter observed aloud, clearly amused.

"I should probably head back to my own office now," he changed the subject. If this conversation went any further, Riese would most likely start teasing him. And if memory served Marty right, she would be relentless in doing so. She may be a practicing lawyer now but he could tell in the short time they'd spent together today that Riese was still, more or less, the same mischievous teenager who used to pester him back in Chicago. "If you need anything else, I'm just down the hall to the left."

"Good to know," she nodded, that all too familiar mocking smirk still plastered upon her lips. "See you around, Martin."

"See you around, Riese," he waved before heading out the door towards his own office.

* * *

The rest of the work day was fairly uneventful for Marty since most of his work had already been finished earlier in the day, so he spent that time reviewing various proposals and reports that had been previously looked over a dozen times. All in the unlikely case that something had been missed. He was so immersed in the process that when there was a knock at his office door, Marty couldn't help but jolt in surprise.

"Sorry about just showing up out of nowhere like this, Dad," his daughter apologized upon entering. "But Laura is already gone and I didn't feel like waiting out there by myself."

"You never need to apologize for showing up unannounced, Winn," he smiled. "How was school?"

"Better, now that I'm not seated by Milly in every single class we share," the teenager answered with a shrug. "Even though I still have to deal with her in the Franklin, it's gotten easier to deal with her snarkiness when she's not right beside me for the entire day."

"You two will get over this," Marty assured his only child. "It's not like this is the first time you've had a falling out with her."

"I don't know, Dad," Winn sighed. "She seemed pretty adamant on not wanting to have anything to do with me. At least, not outside of class." She ran a hand through her hair before sighing again. "I don't feel like talking about this anymore. Can we head home soon?"

"Yeah, just let me close these files and then we'll go," he stated.

As the father and daughter duo made their way down from his office, Marty could not help but feel bad for Winifred's current dilemma. It couldn't be easy being on the outs with a close friend, especially one who has known you for your entire life.

"Hey, weren't you supposed to meet your new head of legal today?" Winn asked all of a sudden.

"Yes, I did," he confirmed, grateful for the break in the oppressive silence that had been dominating their elevator ride to the lobby. "Turns out she's an old friend from when I worked in Chicago."

"Oh, really? That's pretty neat," his daughter smiled as the elevator doors opened. "Does Mom know her, too?"

"They met a couple of times," Marty nodded before gesturing to the person question, who was standing ahead of them in the lobby. "But if you don't believe me, why don't you ask her yourself?"

"Oh, you're still hanging around, I see," greeted Riese with a friendly smile. "Not that I should be surprised though. You always have been quite dedicated in your work." The lawyer then glanced at the teen standing beside him, her expression questioning. "And who is this beautiful young lady accompanying you, Martin?"

"Riese, this is my daughter, Winifred," he introduced with no shortage of pride in his voice. "Winn, this is Riese Jacobs, our new head of legal."

"Daughter? Wow, I didn't realize that you had children," a nonplussed Riese stated, looking completely taken off guard by the fact. "And how old are you, Winn? I mean, if you don't mind me asking, that is."

"I'll be sixteen at the end of November," the teen answered, curt and concise. "And I prefer Winifred, if you don't mind."

"Winifred it is then," the older woman nodded, seemingly impressed. "I must say, you look very much like your father."

"Funny, everyone tells me that I look more like my mom," Winn countered. "I believe you know her."

"I do?" Riese questioned, a delicate eyebrow raised.

"Yes, her name's Rory Gilmore," the teenager continued in that same concise, curt tone. "Sorry, I mean Rory Gilmore-Harrison, I should say."

"Yeah, I know your mother," the lawyer noted aloud, her cheeks now flushed for some reason. "Well, it was very nice to meet you, Winifred." She turned toward Marty, who'd been silent during the entire exchange. "I'm going to head home now. I still have a ton of unpacking to do, so I'll see you tomorrow, bright and early, Martin."

"Alright, see you later, Riese," he waved at the now retreating woman's back. When they were once again alone, Marty turned to reprimand his daughter for how rude she'd been to Riese. "Do you mind explaining to me what that was all about, young lady?"

"I don't like her," she stated, arms crossed over her chest in a petulant manner.

"What? You just met her," Marty pointed out, thrown for a loop by his usually friendly, if somewhat timid, daughter's statement. "Why?"

"Really, Dad? You really need me to spell it out for you?" Winn narrowed her azure eyes up to meet his own hazel coloured gaze.

"Spell what out? I'm not following what you're trying to say," he admitted in honesty.

"You know what? Forget it, let's just leave it at me not liking her and head home," the teen sighed, clearly uncomfortable now. "I am not discussing this any further."

"Winn, come on," Marty pleaded as his daughter began walking away.

"Seriously, Dad, I love you to bits," Winn stated over her shoulder upon reaching the exit doors. "And I think that you're one of the most brilliant people I've ever met, but Grams is right. You can be so incredibly dense sometimes."

With that said Winifred left her shocked father standing alone in the lobby of the Thompson Group, wondering what the hell had just happened.

* * *

Months would pass before Marty discovered the reason behind his daughter's immediate dislike of Riese Jacobs. By then though it would simply be one of the many things that were putting a strain on not only his relationship with Winifred but his family as a whole.

The minuscule cracks in Marty's life that he'd been blissfully unaware of were about to become gapping chasms, and there was nothing he could do to stop it.

* * *

 **Sorry about the long hiatus, good readers. Thank you for your patience. If you could be so kind as to leave a review, that'd be great. Thanks!**


	3. Faces Old & New

**3 - Faces Old & New**

Friday night dinners were not Winn's ideal way of starting off the weekend, but it was what she signed up for when the then high school freshman had agreed to her great grandmother's offer of paying for Chilton.

It was not a popular decision with her parents, nor did her grandmother Lorelai approve. In the end though they all had to accept it when Winn pointed out that this was her future at stake, and it would be foolish to not use every means available for her to get the best education possible.

Her father, of course, was the first to respect her wishes. As someone who had gotten into Yale almost entirely through scholarships and hard work, her father knew what it took to get a high level of education and actively encouraged his daughter to use every opportunity available to gain it. He also warned her not to become dependent on the Gilmore reputation, to use it sparingly and only when absolutely necessary. Too many times had he witnessed some of his more affluent classmates become failures because they tried to use their family name instead of actually putting in the needed work to succeed on their own terms. This was a sentiment which both her mother and grandmother echoed when it became apparent that Winn was not about to change her mind on the subject.

Her first year at Chilton had been a breeze in comparison to her mother's if the stories Winn had heard were to be believed. The amount of schoolwork she'd been given was quite a transition but Winn quickly overcame that obstacle. She was the daughter of Martin Harrison and Rory Gilmore-Harrison after all, so the teen was no stranger to the notion of hard work and dedication.

If only the social side of attending Chilton was as easy to handle as its academic aspect, then Winifred would be set for success.

 _It's all that stupid Davis McCrae's fault,_ the miserable teen fumed, her mind not at all in the present. _If he hadn't dumped Milly only to immediately turn around to ask me out, I wouldn't be in this mess! And why on earth would he even think I'd do that to Milly? She's one of my oldest, dearest friends!_ Winn stabbed at her food without any intention of eating it, her appetite gone thanks to her current train of thought. _Or at least she used to be one of my dearest, closest friends_.

"Stupid bastard," the teenager swore under breath, completely unaware that she'd done so until eventually noticing how the other three people at the table were now staring at her in surprise. "I said that out loud, didn't I?"

"Afraid so, kiddo," her mother confirmed from Winn's left.

"Any chance that we could all forget I said that?" Winn queried, hopeful.

"Probably not."

"Probably not," the teen sighed in resignation, awaiting the inevitable chastening from the ever proper Emily Gilmore.

"Winifred Lorelai Gilmore-Harrison," her great grandmother admonished, right on cue. "There is a time and place for such language but this dinner table is not one of them. I hope you will take care to remember that in the future, young lady."

"I'm sorry, Grams," Winn apologized.

"Now, may I ask who you were muttering about just now?"

"No one important, Grams," lied the hurt teen, not wanting to talk about it. Barely five months had passed since the whole mess started and it still felt far too fresh to discuss.

"Is this still about that McCrae boy? The one who broke up with your friend to pursue you?" Emily pressed.

"Could we not talk about this?" Winn begged. "Please?"

"I don't see why-"

"Grandma, please," Rory interjected on her daughter's behalf. "Can't you see how upset she is?"

"Very well," the elderly woman sighed after a moment of consideration. "I apologize, Winifred, but allow me to say this; if this boy is still bothering you now or anytime in the future, do not hesitate to tell me and I will take care of it."

"You're not going to put a hit out on him," Winn quirked an eyebrow at her great grandmother. "Are you, Grams?"

"If that's what takes for you to be happy again, Fred," a serious sounding Emily stated before smirking over at her great granddaughter, whose mouth was agape in shock. "Then maybe I will."

"I didn't realize I married into the Corleone family," her father deadpanned, which brought a snicker from his wife and an amused eye roll from Winn. "Neat."

"Correct me if I'm wrong, Rory," Emily began, an amused smile on her lips. "But did you not also go through a similar situation with Paris when you attended Chilton?"

"Really?" Winn raised her brow at that, more than a little surprised. "You and Aunt Paris? That's so weird!"

"Paris is weird," her father piped in, never one to miss making a joke at the expense of his wife's friend.

"Regardless of that fact," the Gilmore matriarch intoned. "I believe Paris liked a boy who liked your mother, which caused some friction between them for quite some time."

"Yeah, that wasn't much fun," a cringing Rory agreed, her attention now turned toward Winn. "You think your Aunt Paris is intense now, you should've seen her back when she was in Chilton. Woo, boy!"

"I know the boy was Janlon Dugray's grandson but I forget what his exact name was," Emily pondered aloud, index finger on her chin. "Dustin, maybe? Or was it Justin?"

"Tristan," the only male at the table supplied, much to the surprise of both Winn and her great grandmother.

"Now how in the world could you possibly know that, Martin?" Emily regarded him with genuine curiosity. "Because, correct me if I'm mistaken, I was under the distinct impression that you did not meet Rory until you both attended Yale."

"No, Emily, you're right," he answered. "I didn't meet Rory until Yale."

"Then how do you know about Tristan? If I may be so bold to ask," she pressed.

"I won't bore you with the details because, well, they're no longer important," Winn's father stated flatly. "Just know that I met him a year or so after I graduated Yale and had moved to Chicago. We did not get along."

"Fair enough," the usually dogged Emily nodded, somehow knowing that her granddaughter's husband wouldn't elaborate any further on the subject. That, or the elderly woman simply didn't really care enough to know more.

"Anyhow, the whole mess between Paris and I eventually resolved itself when Tristan was sent away to military school," Winn's mother segued. "As I'm sure things between you and Milan will work itself out." She patted the teen's hand lightly. "I promise."

"I hope you're right, Mom," Winn sighed, dubious. "But unless Davis is somehow expelled in the next few months, I highly doubt it."

"Maybe putting a hit out on this kid isn't such a bad idea after all, Emily," her father deadpanned, which brought an amused scoff from the Gilmore matriarch.

"I know it doesn't happen very often but you two are terrifying when you're in agreement on something," Rory told both her husband and grandmother in a worried tone.

"Eat your peas, Rory," a serenely sinister Emily smiled at her granddaughter.

 _Completely and utterly terrifying,_ Winn silently agreed with her mother.

* * *

"One of these days, I'm going with you to a Friday night dinner," declared Leah Van Gerbig, her head thrown back in laughter.

"I'm glad to see that my weekly awkward family dinners sound like so much fun to you," Winn furrowed her brow. "Which makes me wonder how deprived of entertainment you are at home to actually want to come with."

"It's not that I'm deprived or anything but all my parents talk about at dinner is music, music, and, you guessed it, music," the other girl complained. "A little change in conversation and venue would be nice every once and a while, you know what I mean, Pooh?"

"I told you not to call me that," the taller teen admonished, albeit halfheartedly due to its futility.

"You were more fun before Milan broke up with you," Leah joked.

"You make it sound like we were dating each other," Winn laughed at the absurdity of her friend's remark.

"Well, she is acting more like a spurned lover than a hurt friend," the other girl pointed out, not for the first time. "And don't say that it's because she got dumped. We both know that she wasn't happy with the relationship and was thinking about ending it for quite a while before everything went down like it did."

"Yeah, well, Milan is her mother's daughter," stated Winifred, matter-of-factly. "And we both know how crazy intense Aunt Paris is. Mix in some hurt and anger with that inherited intensity, and, poof, watch the implosion!"

"You know, I usually love drama but not when it hits so close to home," Leah stated, then pointed off towards Kim's Antiques. "Anyway, I'm going to visit _Oe Halmeoni_. See you later, Winn!"

"See you later, Leah," she waved at her departing friend, who returned it in kind before rushing inside the house. Now alone Winn raced ahead towards Luke's Diner, where she whipped the door open upon her entrance. "Abigail Lydia Mariano!"

"Easy with the full name there, Winifred Lorelai," a short blonde waitress retorted from behind the counter. "Or I'll be forced to give you decaf."

"You wouldn't dare!"

"Try me, Gilmore-Harrison."

"You win this round, Turnip," Winn narrowed her eyes at her cousin, only to barely dodge the expected projectile in time. "Yikes!"

"That's what you get for-" Abby began to smugly say before letting out a surprised yelp at the dope smack she'd just received. "Ow! Dude, what the heck you hitting the back of my head for?"

"First off, don't call me 'dude'," Luke told the girl. "Second, don't be throwing the donut bits at customers, regardless of how annoying they're being."

"Hey, that's hurtful!" Winn protested.

"Thirdly, if you're going to waste food like that, make sure you actually hit your target," he continued like the teen hadn't spoken. "Your aim is worse than Kirk's."

"Hey, that's hurtful!" Kirk cried from his seat at the counter.

"And you, go sit down with your mother and grandmother," Luke told Winn, gesturing to where his amused wife and equally amused stepdaughter were seated. "They already ordered for you."

"Man, I think you gave me a concussion," Abby complained in a purposely overdramatic fashion. "I'm totally seeing stars, yo!"

"Stop talking like that, Abigail, you sound ridiculous," he pointed at the coffee machine. "Now do a round then go eat something. Knowing you, you probably skipped breakfast before coming to work this morning."

"You got it, Gramps," the short blonde piped up, suddenly cheerful.

"Every damn Saturday, it's the same damn thing with those two," Luke could be heard muttering on his way back into the kitchen. "Those kids are going to be the death of me!"

"Morning, guys," Winn greeted her mother and grandmother upon reaching their usual table. "Enjoy the show?"

"I really wish you two wouldn't rile Luke up like that," Lorelai chided.

"Sorry, are we stealing your job again, Aunt Lorelai?" Abby joked, now seated next to her.

"Yup, you're definitely Jess Mariano's kid," she glanced sidelong at her fifteen year old grandniece.

"You say that like it's a bad thing," the petite blonde grinned, who then snatched a fry from Lorelai's plate. "Thanks!"

"Definitely Jess' kid," laughed Rory at the older woman's shocked expression while Abby happily chewed the pilfered food.

"So any shenanigans happen before I showed up? Or were Abby and I the opening act?" Winn chirped, taking the empty seat next to her mother.

"Other than Kirk being his usual strange self, nothing's really happened," Lorelai answered.

"I can hear you," Kirk complained from the counter.

"I don't care," singsonged Lorelai.

"Aw, poor Kirk," Rory said. "Everyone picks on him."

"You need a hug, Kirky?" Abby almost purred, obviously unable to resist the temptation of messing with him.

"Yeah, you need a hug, big guy?" Winn joined in.

"I'm a married man," the odd, gangly man stated in near panic, his cheeks red in embarrassment.

"Stop being mean to Kirk, you guys," Rory admonished the now giggling teens. "You know he flusters easily."

"Thank you, Rory," he said, grateful.

"Besides, he's always had a thing for Mom, so you girls are wasting your time," she added with a grin.

"That's it, I'm leaving," an indignant Kirk cried before dropping a twenty dollar bill on the counter and walking out.

"Wow, I didn't know you had that kind of evil lurking inside you, Aunt Rory," Abby clapped, truly impressed. "Bravo."

"I have my moments," Winn's mom shrugged, nonchalant.

"You know, Kirk only asked me out the one time, so I don't think that constitutes as a thing," Lorelai spoke up.

"These pancakes are delicious," Winn stated between bites of her breakfast.

"Blueberry overload?" Abby inquired.

"Hmm-hmm," nodded the older girl, her mouth now once again stuffed.

"You're such a kid," the blonde teased before digging into her bacon and eggs, which Luke had just now placed in front of her. "Thanks, Grandpa Luke. You're the best!"

"You're welcome," he grunted while walking back into the kitchen.

"I'm his favourite," Abby declared.

"That's debatable," a familiar voice stated from the back doorway.

"Billy!" Winn and Abby cried out at the same time, both girls rushing up from their seats so fast that the table shook when one of them bumped it.

"Hey, easy now, guys," their eighteen year old uncle laughed at being tackled. "I missed you, too, but are you trying to kill me?"

"When did you get in?" Abby asked back, ignoring his question.

"How's April doing in California?" Winn chimed in.

"Did you see Dan and Sarah, too?"

"Did you bring me back a seashell?"

"Yeah, did you bring us anything?"

"Oh, I see how it is," he grinned. "You're not actually happy to see me, you just want stuff!"

"Of course!" Both girls chirped in unison, which resulted in hysterical laughter from all three of them.

"Alright, alright, you two, give him some breathing room," Rory cut in, having risen from her chair to join them. "Where's my hug, little brother?"

"Hey, Rory," the tall young man hugged her. "How's Marty doing?"

"Come have dinner with us tonight and you can find out for yourself," she told him.

"Alright, but only if you convince him to cook his famous lasagna," he agreed.

"I'll text him now," Rory turned towards the table where she'd left her bag.

"Hey, Mom," he greeted Lorelai, who'd been strangely quiet this entire time.

"William," she returned, polite but extremely stiff.

"Still mad, huh?"

"I'm not getting into this with you again," a now obviously upset Lorelai rose from her chair. "I'm glad that you got home safe from your _precious_ cross country trip, William, but this-" she gestured between them. "-is something best discussed in private. See you at home." With that said, Lorelai swept out of the diner without another word.

"I think it's safe to say that we're both going to get yelled at when we get home," stated Luke, who'd come out of the kitchen to see what all the ruckus had been about.

"Having me crash upstairs last night was a good call," Will noted.

"I know," his father clapped him on the shoulder. "It's good to have you back, kid. Welcome home."

"Thanks, Dad," the younger man nodded.

"Abby, finish up your breakfast then back to work," the diner owner ordered his nephew's oldest daughter. "Will, sit down and I'll grab you something to eat before you go face the firing squad that is your mother."

"Sorry you had to see that," William apologized to his sister and nieces upon sitting down. "But I honestly thought Mom would be over our argument by now."

"Hey, I've been where you are," Rory said, sympathetic to her brother's plight. "Just be glad she's still talking to you, kiddo."

"I suppose you're right," he conceded.

"Um, I've been meaning to ask," Winn began, uncertain. "But why is grandma mad at you again?"

"I'll tell you later," her uncle promised, suddenly looking very weary. "Okay, Winn?"

"Okay," the teenager nodded, not wanting to press the issue. The last thing Winn wanted to do was make her beloved uncle feel worse than he already seem to be feeling. The teen glanced at the others seated at the table and she couldn't help but notice the now much more subdued atmosphere that had replaced the raucous one when William had first made his presence known.

 _So much for the happy reunion,_ a morose Winn sighed in resignation.

* * *

Dinner with her uncle had gone well enough for Winn on Saturday, who finally got the details to why her grandmother was so upset with William. The whole thing didn't make much sense to the teen though. She understood where Lorelai's fears were coming from, of course, but the reason why Will was taking a semester off was different than Rory's had been.

 _I really don't envy Uncle Billy right now,_ the teen decided while walking through the halls toward her locker. Everybody knew how stubborn Grandma Lorelai could be.

After retrieving the book she needed for her final class of the day, Winn rushed in its direction as swiftly as possible. Without actually running, of course. She was part Gilmore after all. About halfway to the classroom she chanced a look down at her watch before hastening her pace, only to bump hard into another person upon turning the last corner towards her destination. The collision sent them both tumbling to the floor.

"I'm so, so sorry," apologized Winn in a panic. "I shouldn't have taken that corner so swift like that but I'm almost late for class, so I-"

"No, no, no, ah completely understand," interrupted the other person, who turned out to be a curly haired blonde girl around Winn's age. "Ah wasn't exactly being all that careful mahself. Ah have no idea where half my classes are, so ah've been totally lost all day!"

"New girl, huh? I've been there," Winn said, sympathetic. "Which class are you looking for?"

The new girl frowned. "Weren't you running behind?"

"I'm going to be late now anyway, so I might as well help you out," she answered in honesty.

"Sorry about that," the blonde apologized.

"No biggie," Winn lied, dismissive.

"Still, sorry all the same."

"So?"

"Oh, right," the new girl cried. "Chinese Literature with Mr. Chen. You know where that is?"

"Well, I should hope so because I was on my way there," Winn laughed. "Let's go."

"I'm Casey, by the way," the blonde girl introduced herself while following close behind. "I just moved here last week, so ah'm still getting used to the place."

"Well, Casey, it's nice to meet you," she smiled over her shoulder. "I'm Winn."

"So, um, Winn?"

"Yes?"

"Is it common practice for some of our classmates to give the new kid bad directions?"

"Let me guess," Winn stopped to face the other girl, which almost resulted in another collision between the girls. "The person who gave you directions, was she about five foot five with strawberry blonde hair and resting bitch face?"

"You know her then?" Casey raised her brow in surprise.

"Oh, I know her alright," she sneered, not at all pleased. "That's Milan fricking McMasters, Chilton's resident Regina George wannabe!"

"Can't say I'm a fan," the other girl commented. "But nevermind that, shouldn't we get moving?"

"Right, let's go," Winn sighed. The pair continued onward to their class, where Winn began to apologize upon entering the room. "I'm sorry we're late, Mr. Chen, but-"

"It's my fault, sir," her new classmate cut in from behind Winn. "It's my first day here and somebody gave me bad directions. If not for Winn, ah'd still be wanderin' the halls like a chicken with 'er head cut off!"

"If that's the case, then I don't see a problem," their teacher stated after a brief moment of consideration. "Don't let it happen again though." He gestured to a pair of desks near the back. "Please have a seat, ladies."

"Thank you, Mr. Chen," they said at the same time, both girls relieved to be let off the hook. After sharing a quick glance, Winn and Casey hurried to their desks.

"Looks like the hicks found each other," stage whispered Milan to another nearby girl, who Winn recognized to be Claudia Grant.

"Don't drag me into your tiff, McMasters," the dark skinned girl told the red head in no uncertain terms. "I have no beef with Winifred or her blonde doppelgänger."

"Is there a problem, Miss Grant?" Mr. Chen asked from the front. "Miss McMasters?"

"No, sir," both addressed girls stated.

"Good," he nodded, then added in a stern tone. "But in case anyone else feels like being disruptive, he or she will be taking the long walk to Headmaster Medina's office. Understood?"

"Yes, sir," the whole class returned.

"Very good," a seemingly satisfied Mr. Chen nodded. "Now please open up the handouts I gave you last class to page twenty, where we will be discussing the historical accuracy of the Battle of Chibi as it is depicted in Luo Guanzhong's _Romance of the Three Kingdoms_." He paused for a moment. "Seeing as you were both late and I do not have an extra copy of the handout at this time, Winifred, you will share your copy with our newest student until further notice. Now pull your desks together." He paused. "But do it quietly."

"Yes, sir," Winn complied before doing as her teacher bid. When she was finished pulling her desk over beside Casey's own, the two girls shared a smile then opened the handout between them to the designated page.

* * *

"And that's the end of our time together," Mr. Chen announced at the sound of the final bell. "I will be expecting all of your assignments finished this Friday, and remember that it counts for twenty percent of this semester's grade so don't half ass it. Dismissed." As all the students began to shuffle out of class, he called out to the late arrivals. "Winifred, a moment of you and your friend's time please."

"Ooh, it looks like the Dixie Chicks are in trouble after all," Milan taunted on her way past.

"Do be quiet, Miss McMasters," their teacher told her.

"Hmph," the red head scoffed over her shoulder.

"Is something wrong, Mr. Chen?" Winn asked in concern once she and Casey were alone with him.

"We all have places we'd rather be right now, so I'll cut to the chase," he explained, his sharp gaze meeting hers. "As Casey here is brand new to our school, she will be a ways behind the rest of you. What I need from you, Winn, is to help her along in this class until she is caught up. Would you be willing to do so, Winifred?"

"Mr. Chen, I don't think-" Casey began to protest.

"I don't see a problem with that, sir," Winn interrupted. "But I'll only do it if Casey agrees."

The two girls shared a quick glance, after which Casey turned to their teacher. "The sooner that I get caught up, the better. I accept your offer, Mr. Chen."

"Good," their teacher nodded. "And since you are starting later, I will be giving you an extra week's extension on our latest assignment. I know that it's not a lot but it's the best I can do, Casey."

"Thank you, sir," the blonde replied. "I really appreciate it."

"Alright, enough," he waved them off. "Go home, you two. See you tomorrow."

"Yes, sir," both girls said at the same time. They then entered the hall where Winn turned to new classmate, who quirked an eyebrow at her.

"Why's you agree to do that?"

"I've been the new girl and I know how much the opposite of fun that is," Winn answered.

"Still, it's weird," the other girl noted.

"Well, I'm weird, so it's just par for the course for me," she joked, shrugging.

"Weird or not, thank you, Winn," the blonde smiled. "You're good people."

"Don't be too quick to trust her, new girl," Milan stated from down the hall. "Winn has a history of letting people down when they need her most."

"Were you just waiting in the wings for an opening to say something?" Casey asked in annoyance.

"Don't say I didn't warn you," the red head stated over her shoulder as she walked away.

"What a drama queen," the new girl called out. She turned back to Winn. "What's her damage?"

"You'll probably hear this eventually, so you might as well hear my side," Winn began. "Come on, I'll tell you on our way out."

* * *

"That's just ridiculous!" Casey cried after being told what had led to Winn and Milan's friendship breaking down. "How can she blame you for her ex-boyfriend being an asshat?"

"Beats me," Winn sighed, the two girls now waiting in the parking lot for their parents to pick them up. "I've almost given up on trying to fix our friendship though. Now I just try to avoid her whenever possible."

"Yeah, losing friends suck," the blonde girl said, sympathetic. "But if Milan doesn't want you as a friend, I'll happily take you in."

"How charitable of you," she chortled.

"Well, my Nana Marianne always said you should never be ungrateful," Casey stated in a haughty tone, hand held up over her heart like some sort of southern belle. "Anyhow, there's my ride."

"Is that a Porsche?" Winn asked, her blue eyes wide at the approaching vehicle.

"Yeah, it's my mom's," the other girl sighed. "She hates it though, so my dad drives it more often than not."

"We have an Escape and my mom's old Prius," she told her new friend.

"Cool, I'll see you tomorrow, Winn," Casey waved while entering the Porsche, which was being driven by a handsome blonde man in his early to mid forties. The man who she assumed to be Casey's dad waved at her. Just as they were about drive away, Casey rolled her window down. "Add me online when you get the chance, okay?"

"I don't know your last name though," she cried back.

"Dugray," the other girl shouted before the expensive sports car zipped out of the parking lot.

 _Dugray? Why does that name sound familiar?_ Winn wondered to herself until she noticed her mother's approaching Prius.

"How'd your day go, kiddo?" Rory inquired upon her entrance.

"Great," the teenager answered, genuinely happy. "I made a new friend today."

* * *

Though it was unbeknownst to her at the time, Winifred would soon realize that Casey was much more than just a new friend. And that revelation would change her world forever.

* * *

 **Sorry for the delay but I'm having computer issues, so updates are difficult. As per usual, reviews are appreciated. Thanks for reading.**


	4. Not One Damn Thing

**4 - Not One Damn Thing**

"And where exactly do you think you're going?" Lorelai shouted at her son, who had now turned his back to her. "We are not done talking about this, Will!"

"You may not be but I sure the hell am," he snapped over his shoulder while yanking on his jacket.

"William Richard Danes, you get your ass back in here right now," his mother demanded. "I'm talking to you, damn it!"

"And I'm ignoring you," the eighteen year old muttered on his way out the door. Will had no real destination in mind, he just needed to get away from the argument with his mother before one of them said something they'd both regret.

With his head down and hands stuffed into his jacket pockets, Will meandered down the nearest trail off the street. It didn't take long for him to reach the Stars Hollow bridge, its wooden planks creaking under each step. Lost in thought, Will didn't notice the figure seated near the middle of the wooden span until he was almost right on top of them.

"Shit," he muttered under his breath upon recognizing the person, who was none other than Leah Van Gerbig.

"I heard you were back in town," the girl stated in trepidation, who had risen from her seat on the bridge. "How was your trip?"

"It was fun," a clearly uncomfortable Will shrugged. "I stayed with my sister April in Venice Beach for a week then visited Dan and Sarah up in Portland after that."

"So you had fun then," Leah nodded, whose posture showed she was feeling just as awkward and uncomfortable as Will. "That's good to hear."

"And how was your summer?" he asked, not knowing what else to say.

"Are we really going to keep doing this, Will?" she countered, her brown eyes watery.

"I don't know how to act around you anymore, Leah," the eighteen year old admitted. "Ever since-"

"-I confessed my undying love to you," the younger teen finished, now unable to look him in the eye. "Yeah, I get it, Will. And I don't blame you, especially how I did it right before you left. It was pretty crazy, I know."

"It's not crazy," he shook his head. "And I'm extremely flattered, Leah, but-"

"-but you don't feel the same way," she sniffled.

"I'm sorry," Will apologized.

"It is what it is," stated Leah, her voice unsteady. It sounded like she was barely holding it together right then. "I'm gonna go home now."

"Leah," he began to reach out, only to stop when the girl took a step back.

"We would never have worked anyway," she shook her head. "You're two years older than me and about to head off to college. You can't be held down by some high school aged girlfriend, right?"

"Right," he lied, not having the heart to tell her otherwise. The truth would simply hurt her more, and it was obvious that Leah was hurting enough already. No use adding to it now.

"You're a good guy, Will," she smiled sadly before walking away.

"Damn it," Will sighed, almost wishing that he'd stayed home to continue arguing with his mom instead.

* * *

"Wow, it's busy," Will noted upon entering the diner.

"Your observational skills are on another level, kid," his dad deadpanned while rushing past, several plates expertly balanced on his forearms. "Weren't you supposed to be helping your mom at the Dragonfly today?"

"Yeah, about that," he rubbed the back of his neck.

"You two got in another fight," Luke deduced in exasperation, each plate now placed down on a nearby table. "Enjoy your meal, folks," he said to his customers before turning back to Will. "Upstairs. Now."

"Dad-"

"No discussion, Will," he interrupted in an unusually calm voice. "Go."

"Alright, fine," the eighteen year old sighed in resignation, not at all looking forward to the lecture that his father was about to give him.

Moments later had Will up the stairs in the his father's old apartment, his eyes drawn to all its old furniture and such that were still set up. He could never understand why his father insisted on keeping the place somewhat well furnished. Sure, Jess and his family had lived here for a time until buying their house on Plum Street, but that was almost seven years past now. Other than his overnight stay upon arriving in Stars Hollow a few days ago, no one had occupied the space since then. At least, not according to the thin layer of dust on most of the furniture.

Before he could ponder that line of thought any further, his father's heavy steal toed boots could be distinctly heard thumping against the wooden stairs. It did not take long for Will to come face to face with a less than pleased Lucas Danes.

"I know I said before you left on your trip that I wasn't going to get involved with this disagreement between you and your mom, but it looks like I no longer have a choice in the matter," he began to rant, which was definitely not that fun to be on the receiving end of. "I thought if I gave you two some time to cool off, some distance to realize that you were both being complete stubborn idiots, you'd see where the other was coming from, but no, both of you insist on being...complete stubborn idiots!"

"Dad-"

"Shut up, I'm not done talking," his father barked, the scowl on his face telling the younger man that now was not the time push his luck. Despite being in his mid sixties, Luke Danes was still the same broad shouldered, intimidating looking man he'd been when Will was a boy.

"Sorry, sir," he apologized.

"No, no," he growled, a hand now on pressed against his forehead in an attempt to calm himself. "I'm sorry, Will. I just...for the last three months, all I've heard is your mother complain about how stubborn you are, how you're making a huge mistake taking freshman year off, and all I can think of is how she cut Rory out of her life when she dropped out of Yale. I really don't want that to happen between you and Lorelai."

"They got better," the younger Danes pointed out, albeit it was done halfhearted.

"Your mother is the most stubborn person I've ever met," Luke stated like he hadn't heard. "And I'm not exactly all that compromising either, so I guess it shouldn't be all that surprising you are how you are when you make up your mind."

"Was that a compliment?" Will joked, again halfhearted.

"Now's not the time for jokes, Will," the older Danes stated, solemn. "This is a serious problem, and it needs to be dealt with."

"I know, Dad," he conceded, running a hand through his charcoal hair. "But I'm at a complete loss on what to do. Whenever you're not around to keep the peace, Mom just starts-"

"Wait a second," his father cut in, his expression one of a person having an epiphany. "I have an idea! What if I didn't have to be there to keep the peace? Or rather, you didn't have to be there?"

"Come again?" Will frowned, not quite following.

Instead of answering with words, his father gestured at their surroundings.

"Oh, you're kicking me out," an unamused Will concluded, succinct.

"Yes...and no," answered a grinning Luke Danes before going into detail with his plan.

* * *

After having spent the last half hour or so hammering out a rough rental agreement with his new landlord and boss (aka, his father), Will decided that there was no better time than the present to begin fulfilling one aspect of said agreement.

"So that's two specials and a mozza burger with fries then," he wrote down the order with a deft hand. "Anything to drink?"

After that was finished Will headed over to post the ticket for Caesar, who was manning the kitchen, then he grabbed the coffee pot to make a refill round the diner, which was only about half full. While he was doing this, the younger Danes thought back on what had transpired upstairs earlier and couldn't help but smile in amusement. Will wasn't an idiot. He was fully aware on what his dad was doing. It was obvious, really. Obvious and, admittedly, quite ingenious. Will seriously hoped his mom would agree to the arrangement as well.

"Be right with you," the young adult called out at the sound of the bells jingling, which meant somebody had just entered the diner.

"Alrighty," a feminine voice cried back with a slight twang.

Intrigued by the unusual accent, Will glanced over to discover that the new customer was an attractive young blonde around his age, maybe a little younger. He quickly finished his latest coffee round before heading over to stand in front of the girl, who simply regarded him with a friendly smile.

"May I help you?" Will raised an eyebrow at her.

"If you have a blueberry muffin and some super strong coffee, then yes, you can certainly be of great assistance," she grinned cheekily.

"You're not from around here," he commented. "Are you?"

"Your observational skills are quite astounding," the girl teased.

"So I've been told," an amused Will deadpanned, pouring a cup of coffee for her then setting it on the countertop.

"Thank you, good sir," she sipped at the hot beverage.

"No problem. Let me grab you that muffin," he turned away to do so.

"So what do the kids in this town do for fun?" the girl asked.

"Oh, you know, the usual," Will deadpanned while placing the blueberry muffin in front of her. "Arson, burglary, jaywalking."

"Ooh, jaywalking, that's too crazy for me," she stated in mock seriousness. "A lady's gotta draw the line somewhere."

"That's completely understandable," he chuckled, quite taken in by the girl's wit and charm.

"Order up!" Caesar cried from the kitchen.

"I'll be right back," Will promised, silently cursing Caesar for his bad timing.

"Ah'll be here waitin'," the blonde drawled, delicately breaking a piece of her muffin off to eat.

"Mrs. Resnick, table three," the longtime cook told Will, who simply nodded back before delivering the food to its destination. He shot the blonde at the counter a quick smile on his way past, which she returned with a brilliant one of her own.

"Who's your new friend, William?" Mrs. Resnick inquired when he arrived at table three, the plate now set in front of the elderly lady.

"I haven't got a clue, Mrs. Resnick," the young man admitted

"She's very pretty," the elderly woman pointed out, unnecessarily. "And seems to like you, too. You should find out."

"Thanks, Mrs. Resnick," he chuckled. "I'll get right on that."

"See that you do, dear boy," she patted his forearm with affection. "See that you do."

With that finished Will returned behind the counter, ready to resume his conversation with the mystery girl, only to have his attention drawn to the ringing bells on the front door.

"Hey, sorry I'm late but my tablet was being all fritzy. My dad managed to fix it though, so it's all good," his niece fired off in that trademark Gilmore fashion. "Hope you weren't waiting too long."

"Was I supposed to meet you?" Will frowned, thoroughly and utterly thrown.

"Oh, hey, Billy!" Winn greeted, her wide smile now directed at him. "No, I was talking to Casey. Sorry about that."

"Oh, so you do you have a name," he remarked to the blonde.

"We'd have gotten 'round to it eventually," she waved it off.

"Anyhow, we have school work to do, so we'll see you later, Billy," his niece turned to leave. "Come on, Casey, we have the house to ourselves for the next two hours, so it'll be perfect for studying!"

"I'll be right out," the blonde called over her shoulder. Their gazes met again. "So what do I owe you?"

"First one's on the house for new customers," Will told her. "It's the rule."

"Oh, really?" Casey quirked an eyebrow, skeptical.

"Yes, really."

"I like that rule."

"Figured you would."

"Well, rule or not, thank you for the coffee and blueberry muffin," Casey said, turning to leave and join Winn outside. She paused at the door then glanced back to smile at him. "See you around, Billy."

"See you around, Casey," he smiled back, basking in the moment.

"Ugh, teenagers," Caesar groaned from the kitchen, obviously having caught the whole scene.

"Such a killjoy," an annoyed Will complained, the moment now officially gone.

* * *

"Yeah, I'll tell him, boss. No problem, I can close up by myself. Been doing it for years now," said Caesar into the telephone, obviously speaking to Luke on the other end. "Alright, goodnight." He hung up the receiver, their conversation over just like that. "Hey, Will, your dad wants you home ASAP."

"Any particular reason why?" Will inquired, broom still in hand.

"Not really," the rotund cook shook his head. "Just something about what you two talked about upstairs this afternoon."

"You good closing by yourself? Because I can stay if you need help," he offered.

"Go home, kid," Caesar waved him out. "I got this. No worries."

"I'm just going to grab my jacket then go," Will hiked his thumb toward the storeroom where he'd left his coat. Moments later had him outside, the eighteen year old's hands in his pockets as he meandered back home. Will had made it a few meters passed the gazebo when he heard his name being called out from across the square. A smile immediately came to his lips upon noting whom it was approaching him. "Hey, still around I see."

"Yeah, but not for long, ah'm afraid," Casey informed. "My dad's going to be here any minute. Still find it weird that he didn't even need directions to know how reach Stars Hollow but whatever." She paused to shoot him a megawatt smile. "Finally done work, huh?"

"You're very astute," he teased.

"Why thank you, William," the young blonde giggled. "How kind of you to notice!"

"No problem," he shrugged.

Both teens stood face to face in comfortable silence, his stark blue eyes meeting her sea foam green, the pair simply exchanging affectionate smiles for who knows how long until finally somebody just had to intrude on them.

"So, are you two just going to stand there and stare at each other like idiots all night?" Abigail Mariano sneered, arms crossed over her chest in an impatient manner. "Or you going to get the hell out of our way?"

A bemused Will briefly wondered at his niece's tone before noticing the person standing next to the petite blonde, which made him want to curse at his crap luck.

"Hey," a hurt Leah waved, those big chocolate coloured eyes round and watery.

"Hey," a guilty Will returned, weak and nearly inaudible.

"Hey," a confused Casey piped in.

"I'm Fat Albert," quipped an impatient Abby. "Now could you two get off the damn sidewalk so we can get by already?"

"Oh, right, sorry," apologized the taller of the two blondes, her hand now grasping Will by the wrist to lead him aside.

"Thanks," his niece trudged along with a sluggishly moving Leah in tow.

"What was that about?" Casey asked when they were once again alone. "'cause let me tell you, that was tense!"

"It's complicated," he sighed.

"Lemme guess, the angry little blonde is the cute Asian girl's best friend," the new girl deduced aloud. "And by the way she looked like she was going to start crying any second, cute Asian girl is your...ex-girlfriend?"

"Pretty close," Will sighed again. "The blonde is my niece, Abby. The other one was Leah, her best friend. She asked me out, I said no. And now-"

"And now things are awkward," Casey finished, astute. It seemed as though the curly haired blonde was going to say something further on the matter but the honking from an expensive looking sports car cut her off. "Oh, there's my ride. I've got to go."

"See you around," he waved, trying to hide his disappointment.

"Yes, you will," she promised with a softer, more genuine smile than her earlier, flirtatious ones. "Goodnight, William."

"Goodnight, Casey," a now more hopeful Will whispered back, the girl already too far away to hear him. As the Porsche passed by though the blonde had her hand pressed up on the glass, those green eyes still visibly expressive even from a distance. Unable to think of anything else to do, Will simply waved again. Once more by himself, the eighteen year old began the trek home where his parents were awaiting his arrival.

* * *

Unaware of it at that moment, Will would soon come to know how it was to fall madly in love for the first time in his young life. Unfortunately, he would also come to know how it felt to have his heart broken for the first time as well. But, to tell the truth, there wasn't one thing Will would change about it.

Not one damn thing.

* * *

 **Okay, just one more POV character to introduce after this, then it's back to Rory. Thanks again for reading, and feel free to leave a review.**


	5. The Joy & the Shame

**5 - The Joy & the Shame**

After losing sight of Will in the town square, a conflicted Casey leaned back into her car seat and let out a frustrated sigh.

"That's not a happy noise," her dad remarked. "Did your study session not go well?"

"It went fine," she murmured.

"Then what's with the long face?" he pressed.

"It's nothing," Casey lied.

"Oh, this has to do with that boy you were talking to when I arrived," he deduced.

"How long were you sittin' there watching before beepin' the horn?" she narrowed her eyes at him, unamused.

"About thirty seconds," he shrugged. "A minute at most."

"You are so very weird sometimes," the teen pointed out.

Her father ignored the jibe. "So does mystery boy have a name?"

"Ah'm not having this conversation with you," a mortified Casey cried, face hidden in her hands.

"Better me than your mother," the blonde man stated, matter-of-factly. "Right?"

"Damn it," the teen sighed, knowing that he had a point there. "Will. His name is Will."

"See? That wasn't so hard," he stated, smug in his minor victory.

"Are you kiddin' me?" Casey rolled her eyes. "That was like pullin' teeth."

"Speaking of your mother," her father segued. "You do remember what she thinks about you dating, right?"

"If mom wants to dictate mah life like Nana did hers, then maybe she should try being a part of it rather than gallivantin' 'round the world all the damn time."

"That's not fair, Cas," he chided.

"Yeah, well, life isn't fair, dad," the teen muttered, bitter.

"When did my little girl become so cynical?"

 _Probably around the same time I found out the real reason why you're divorcing mom,_ Casey wanted to say. Instead though she decided to stay silent in order to spare his feelings. Whatever flaws he may possess, Tristan Dugray was still a kind and caring father. He didn't deserve that sort of cruelty, especially not from her. It wasn't his fault that-

"-en to Fall Out Boy?"

"Ah'm sorry," she frowned, completely thrown off her train of thought. "What was that?"

"I asked if you wanted to listen to Fall Out Boy," he repeated.

"Yes, please," Casey nodded, a smile now plastered on her lips. Her father always knew exactly how to raise her spirits, no matter how upset Casey seemed to be at that and almost any given moment.

He returned the smile warmly with one of his own. "Which song first?"

"You have ta ask?"

"Right, my bad," her dad laughed before selecting the appropriate track.

" _They say we are what we are,  
_ _But we don't have to be,  
_ _I'm bad behavior but I do it in the best way,  
_ _I'll be the watcher (watcher) of the eternal flame,  
_ _I'll be the guard dog of all your favorite dreams._

 _Ooh, I am the sand in the bottom half of the hourglass glass (glass),  
_ _Ooh, I try to picture me without you but I can't."_

As her father continued to sing along with Casey's favourite band, the sixteen year old stealthily glanced at him from the corner of her eye and quickly realized how that one line from the song rang true. She really couldn't imagine her life without Tristan Dugray in it.

And it made Casey resent her mother even more than she already did.

* * *

"Hmm, this Liu Bei guy sounds like a real two faced scoundrel," Casey muttered to herself, the copy that Winn had made for her now laid down in her lap while the teen read. "How's he considered one of the heroes again?"

After reading yet another paragraph from the heavy sheaf of papers, a now flagging Casey decided that a break was soon in order. She rose from the couch and placed the handout on top a nearby coffee table along her way to the kitchen. She then pulled her cellphone from her sweater pocket, which Casey deftly unlocked in order to open its music app. With her selection made the teen deposited the device on the countertop before opening the fridge to prepare a snack for herself, softly singing along with the lyrics now coming from her phone's speakers.

"Orange juice or almond milk?" Casey pondered aloud in tune with the music, her sandwich already positioned on a plate beside the still blaring smartphone. "Let's see now..."

As she turned back to face the open refrigerator, the track that had been playing came to its end. Having forgotten that the app was set on random, Casey froze when a familiar song began to play, a song that carried some unwelcome memories.

" _Childhood living is easy to do,  
_ _The things that you wanted I bought them for you,  
_ _Graceless lady you know who I am,  
_ _You know I can't let you slide through my-"_

The sudden interruption of someone calling snapped the teenager out of her trance, the plastic cellphone now clattering noisily against the marble countertop.

"Hello?" Casey greeted without checking the caller ID, trying to ignore how shaky her voice must sound.

"Hey, it's me," Winn returned, concern in her voice. "Are you okay? You sound weird."

"Ah'm fine, just...kind of annoyed," she half-lied. "But never mind that. What's up?"

"Look, if I'm bothering you, I can just talk to you tomorrow at school," the other girl began, apologetic.

"You're not botherin' me, Winn," assured Casey.

"Are you su-"

"You're not botherin' me but ah admit that you are keepin' me from my Swiss cheese, ham on rye right now," the blonde reiterated. "So tell me what's up?"

"Alright, if you insist," her new friend stated. "I was wondering if you'd like to set up another study session sometime this weekend?"

"Sure, that sounds like a great idea," she agreed, now smiling at the prospect of seeing Will again. "Meet yah at the same place like last time?"

"Sounds good," Winn stated. "We'll go over the details tomorrow in Mr. Chen's class."

"Ahright."

"Oh, and one more thing," the other girl said, cheerily. "Try not to flirt with my uncle in front of me, okay? It weirds me out. Good night."

"G'night," a stunned Casey frowned at her cellphone, only to quickly hit the stop button on her music app when the song from before the phone call was about to resume. _I really hate that song. I should take it off my phone eventually._ She shook her head at the thought, then at what her new friend had just revealed about herself and William. "Another niece? Stars Hollow really is a small town, isn't it?"

With a resigned sigh Casey found that she was no longer hungry but she decided to finish eating the snack she'd prepared anyway. It'd be quite the shame to waste a perfectly good sandwich.

* * *

"Ahright, three o'clock tomorrow then," confirmed Casey, her school bag thrown over her shoulder. "Anything else?"

"No, that's it," Winn shook her head. "I am wondering what your hurry is though."

"Sorry if ah seem a bit frazzled," she apologized. "But ah just got a text from my dad. Looks like the package ah've been waiting for finally arrived. Just a little anxious is all."

"Hey, did you colour your hair sometime this week? It looks darker for some reason," her new friend commented, the pair exiting the classroom together.

"Really? Damn, ah'm gonna hafta get my highlights redone," she sighed in annoyance. "Ah hate how bland my natural colour is. It looks like a dirty hay bale is sittin' on my head if ah don't do somethin' 'bout it."

"Sorry, I didn't mean to upset you," Winn apologized.

"Ah'm not upset," denied Casey.

"You're drawling out your 'I' when you speak," the other girl pointed out.

"So?"

"So, I've noticed you only do that when you're excited or upset."

"Ah see astute observations run in your family," Casey rolled her eyes.

"Sorry, I didn't mean to offend you," Winn apologized.

"Don't worry 'bout it," she laughed. "You are not the first person to tell me that. And I seriously doubt you'll be the last."

"If you say so," her relieved friend said. "Is your dad picking you up today?"

"Nah, thought ah'd walk home today, take in the sights, you know? See what my new hometown has to offer me," answered Casey with a wave. "See you tomorrow, Winifred."

"See you tomorrow, Casey," Winn waved back before heading in the direction of her locker.

Now alone on her trek, Casey strode towards the nearest known exit with purpose. Along the way there though, she decided that she needed a drink from the water fountain. Just as the newest student at Chilton had finished slacking her thirst, Casey felt a presence from behind her.

"Cassandra Elise Marianne Walker Dugray," a smug Milan McMasters drawled out, saying the new girl's name like it was an insult. "Daughter of Tristan Dugray and his estranged wife Andrea, though rumour has it that the first part of that equation might be in doubt." The strawberry blonde began to circle her, not unlike a bird of prey about to strike. "Oh, I know who you are, new girl. I've done my homework on you."

"Big whoop, did you want some sorta prize?" Casey sneered.

"Oh, no, seeing you this shaken up is all the prize I need," the shorter girl taunted back. "This is my school, you _Hart of Dixie_ castoff. If you don't want everybody to know that you're some spawn of a groupie, you'd best remember that."

Without another word Milan strode away in triumph while leaving a devastated Casey in her wake.

* * *

In the weeks following this hostile encounter with Milan, Casey would come to discover the true reason behind the other girl's irrational hatred of her. It would be only one of many things in her young life that would further complicate it.

The dominos were all set up, ready to begin their cascade across the floor in a beautiful, cacophonous display. All they needed now was the tiniest of pushes...

* * *

 **Thanks for reading. Reviews are appreciated.**


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